How Was Bob Dylan’s First Interview With Rolling Stone Magazine?

“I don’t want anybody to be hung up… especially over me, or anything I do,” said Bob Dylan his first Rolling Stone interview. At the time, Dylan was one of the most secretive and elusive people in the business. But according to interviewer John Wesley Harding, some of this was meant to never “make a foolish move.”

Bob Dylan | Photo Credit Rolling Stone

Between 1969-era Bob Dylan and today, there is a much different relationship between artists and the press. Back then, there was no real connection between publicity and what a journalist may or may not think about you. Today, in the social media climate that surrounds the globe, it’s quite the opposite.

In 1969, Rolling Stone founder Jann Wenner got his interview with the iconic Bob Dylan, after months of preparation and persistence.

The First Bob Dylan Rolling Stone Interview

Bob Dylan | Photo Credit Rolling Stone

After 18 months of letters, Bob Dylan finally reached out to Jann Wenner. “I met Bob for the first time at another hotel in New York,” wrote Wenner. “He casually strolled in wearing a sheepskin outfit, leather boots, very well put together,” he confirmed. Ironically, this first-hour chat was only about why he should do the interview.

Eight months later, the interview took place on a Thursday afternoon in New York City at the hotel. When asked about this later, Bob Dylan really only could remember the gigantic crowd around the corner for Judy Garland’s funeral. “Bob was very cautious in everything he said,” wrote the interviewer.

Wenner decided to write the interview in a Q&A format, rather than in large chunks like the magazine usually did.

Life On The Road Can Get Messy

Bob Dylan | Photo Credit Rolling Stone

In the first few answers, Dylan gave bite-sized answers. When might he go back on the road? “November…possibly December.” What kind of venues? “Medium-sized halls,” said Dylan. As for the tour, he planned to keep it simple, invite some background girls, but he didn’t know what sound he was going for yet.

Beyond the yes and no answers, he did say he might soon include Marvin Rainwater or Slim Whitman in an effort to showcase them to his audience. In the end, he said he can’t stand to see himself on television, why he hates the movie business, but it generally came off as care-free, yet reclusive.

Finally, he said, “Well, Jann, I’ll tell ya – I was on the road for almost five years. It wore me down. I was on drugs, a lot of things. A lot of things just to keep going, you know? And I don’t want to live that way anymore. And uh … I’m just waiting for a better time – you know what I mean?” said Bob Dylan.

What do you think of this first interview with Bob Dylan and Jann Wenner?

Brock Swinson is a contributor at MMN, Airows, and Creative Screenwriting Magazine. He is also the author of 'How Hollywood Screenwriters Annihilate Writer's Block,' which includes advice from Aaron Sorkin, William Monahan, and Cary Fukunaga. Get it for free or listen to interviews at the "Creative Principles with Brock Swinson" podcast on the website above.